NP-MRD: Showing NP-Card for 8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate (NP0302825)

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Record Information

Version

2.0

Created at

2022-09-10 16:39:04 UTC

Updated at

2022-09-10 16:39:04 UTC

NP-MRD ID

NP0302825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate

Description

8,9,20-Tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]Docosan-18-yl 2-methylpropanoate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. 8,9,20-Tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]Docosan-18-yl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151518182D          

 60 67  0  0  0  0            999 V2000
    2.7355    3.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245    2.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6779    2.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6903    1.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443    0.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4070   -0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872   -0.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8159   -0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9261   -1.8944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6006   -2.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852   -2.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -3.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239   -0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -1.1440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -2.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3915   -2.6490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9636   -2.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7153    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955   -0.7456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5956   -0.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202   -1.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079   -0.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5705    0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5441    0.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3997    1.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2125    1.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483    0.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7920   -0.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5976   -0.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2358   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7312   -1.7494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5030   -2.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2159    0.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485    1.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8007    1.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8258    3.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6402    2.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322    3.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    4.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178    4.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2328    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2053    1.9139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6683    1.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2141    2.1305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129    3.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4979    3.4976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269    3.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515    0.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251   -0.1798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2156   -0.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7616    0.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4989    1.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1587    1.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -1.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2654   -1.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735   -2.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4915   -2.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929    2.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 33  1  0  0  0  0
 18 33  1  0  0  0  0
 23 33  1  0  0  0  0
 33 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 35 42  1  0  0  0  0
 23 42  1  0  0  0  0
 42 43  1  0  0  0  0
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 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 44 49  1  0  0  0  0
  5 49  1  0  0  0  0
 18 49  1  0  0  0  0
 49 50  1  0  0  0  0
 20 50  1  0  0  0  0
  6 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
  4 53  1  0  0  0  0
 53 54  2  0  0  0  0
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 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 55 59  1  0  0  0  0
  3 60  1  4  0  0  0
M  END

     RDKit          3D

112119  0  0  0  0  0  0  0  0999 V2000
   -4.5795   -3.2617    3.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3518   -3.5653    2.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259   -2.2646    2.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4339   -1.4657    3.1375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961   -1.9337    0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9231   -2.8572   -0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6295   -4.0706   -0.2083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6463   -2.3165   -1.3846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586   -0.9157   -1.5391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6475   -0.1404   -0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2677   -0.3364    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2661    0.6425    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2057    1.3480   -0.7657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2744    0.9414   -1.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -0.5305   -1.2053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3105   -1.4220   -2.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765    0.8918   -1.5625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1289    0.8787   -2.7942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6238    1.3463   -3.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505    1.3297   -5.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7779    1.8071   -4.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514    1.7299   -0.5980 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.8833   -0.7244    1.0113 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.9283   -0.6966   -0.0811 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.9068   -3.0477   -0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2572   -4.0867   -1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6627    2.8195   -1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1515    3.7850   -2.7089 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1033    6.2010   -1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7850   -4.1771    3.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2625   -2.4719    3.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4362   -2.9257    2.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6920   -4.1971    3.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801   -4.1225    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0782   -0.7462    3.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6605   -0.7772   -2.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9522    0.7740    1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0634    1.4104   -2.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9093   -1.5791   -3.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004151518182D          

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M  END
> <DATABASE_ID>
NP0302825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(O)=C1C2C34OC5(C)OC3(C(OC(C)=O)C(OC(C)=O)C2(C)C(OC1=O)C1=COC=C1)C1(C)C(CC(=O)OC)C2(C)CC1(O5)C(O)(C2OC(=O)C(C)C)C4OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H52O18/c1-12-23(46)26-27-36(8,28(56-32(26)49)22-13-14-52-16-22)29(53-19(4)43)30(54-20(5)44)42-37(9)24(15-25(47)51-11)35(7)17-39(37)40(50,33(35)57-31(48)18(2)3)34(55-21(6)45)41(27,42)59-38(10,58-39)60-42/h13-14,16,18,24,27-30,33-34,46,50H,12,15,17H2,1-11H3

> <INCHI_KEY>
SQOQPYMECDYHFH-UHFFFAOYSA-N

> <FORMULA>
C42H52O18

> <MOLECULAR_WEIGHT>
844.86

> <EXACT_MASS>
844.315364834

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
82.75035930980562

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.674941493666663

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.736245466374909

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.454531603676141

> <JCHEM_PKA_STRONGEST_BASIC>
-2.862527737966706

> <JCHEM_POLAR_SURFACE_AREA>
239.08999999999995

> <JCHEM_REFRACTIVITY>
196.61270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       5.106   6.531   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.832   5.173   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.999   3.831   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.022   2.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.003   1.082   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.493  -0.378   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.390  -1.606   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.390  -1.507   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.595  -3.536   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.988  -5.100   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.466  -5.335   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.952  -6.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.725  -0.771   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.265  -2.135   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.290  -3.791   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.731  -4.945   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.799  -4.098   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.335   0.397   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.232  -1.392   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.112  -1.568   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.971  -3.321   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.575  -1.387   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.065   0.250   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.882   0.760   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.613   1.998   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.130   2.649   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.144   0.092   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.345  -1.178   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.849  -1.746   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.040  -0.770   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -5.098  -3.266   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.539  -3.809   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.403   0.785   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.397   2.096   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.495   3.106   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.393   4.566   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.408   5.813   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.928   5.568   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.860   7.252   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -3.833   8.446   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.340   7.497   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.435   2.079   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.383   3.573   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.247   2.507   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       2.266   3.977   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       2.264   5.760   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       0.929   6.529   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       3.597   6.532   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       2.336   1.269   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       2.847  -0.336   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       6.002  -0.683   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       7.022   0.472   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       6.531   1.932   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       7.763   2.957   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       6.493  -2.143   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       7.962  -2.604   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       7.977  -4.144   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       6.517  -4.634   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       5.600  -3.397   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       3.347   3.946   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   60                                                  
CONECT    4    3    5   53                                                  
CONECT    5    4    6   49                                                  
CONECT    6    5    7    8   51                                             
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   33   49                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22   50                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   33   42                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   27   35                                             
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   27   18   23   34                                             
CONECT   34   33                                                            
CONECT   35   25   36   42                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   35   23   43   44                                             
CONECT   43   42                                                            
CONECT   44   42   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   44    5   18   50                                             
CONECT   50   49   20                                                       
CONECT   51    6   52   55                                                  
CONECT   52   51   53                                                       
CONECT   53   52    4   54                                                  
CONECT   54   53                                                            
CONECT   55   51   56   59                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   55                                                       
CONECT   60    3                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  134    0
END

View in JSmol

Synonyms

Value	Source
8,9,20-Tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1,.0,.0,.0,.0,]docosan-18-yl 2-methylpropanoic acid	Generator
8,9,20-Tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₄₂H₅₂O₁₈

Average Mass

844.8600 Da

Monoisotopic Mass

844.31536 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(O)=C1C2C34OC5(C)OC3(C(OC(C)=O)C(OC(C)=O)C2(C)C(OC1=O)C1=COC=C1)C1(C)C(CC(=O)OC)C2(C)CC1(O5)C(O)(C2OC(=O)C(C)C)C4OC(C)=O

InChI Identifier

InChI=1S/C42H52O18/c1-12-23(46)26-27-36(8,28(56-32(26)49)22-13-14-52-16-22)29(53-19(4)43)30(54-20(5)44)42-37(9)24(15-25(47)51-11)35(7)17-39(37)40(50,33(35)57-31(48)18(2)3)34(55-21(6)45)41(27,42)59-38(10,58-39)60-42/h13-14,16,18,24,27-30,33-34,46,50H,12,15,17H2,1-11H3

InChI Key

SQOQPYMECDYHFH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Mexicanolide
Prostaglandin skeleton
Eicosanoid
Hexacarboxylic acid or derivatives
Naphthopyran
Naphthalene
1,3-dioxepane
Carboxylic acid orthoester
Delta valerolactone
Dioxepane
Delta_valerolactone
Ortho ester
Oxane
Fatty acyl
Pyran
Meta-dioxane
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Heteroaromatic compound
Tertiary alcohol
Furan
Cyclic alcohol
Meta-dioxolane
Orthocarboxylic acid derivative
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Enol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.7	ALOGPS
logP	2.67	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.45	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	239.09 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	196.61 m³·mol⁻¹	ChemAxon
Polarizability	82.75 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76184138

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate (NP0302825)

MOL for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)

3D MOL for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)

3D SDF for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)

3D-SDF for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)

PDB for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)

3D PDB for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)

SMILES for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)

INCHI for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)

Structure for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)

3D Structure for NP0302825 (8,9,20-tris(acetyloxy)-6-(furan-3-yl)-19-hydroxy-3-(1-hydroxypropylidene)-16-(2-methoxy-2-oxoethyl)-7,12,15,17-tetramethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]docosan-18-yl 2-methylpropanoate)